SE455096B - 4,5,6,7-tetrahydrotiazolo /5,4-c/-pyridinderivat, forfarande for framstellning derav samt farmaceutisk komposition innehallande nemnda derivat - Google Patents
4,5,6,7-tetrahydrotiazolo /5,4-c/-pyridinderivat, forfarande for framstellning derav samt farmaceutisk komposition innehallande nemnda derivatInfo
- Publication number
- SE455096B SE455096B SE8406338A SE8406338A SE455096B SE 455096 B SE455096 B SE 455096B SE 8406338 A SE8406338 A SE 8406338A SE 8406338 A SE8406338 A SE 8406338A SE 455096 B SE455096 B SE 455096B
- Authority
- SE
- Sweden
- Prior art keywords
- pyridine
- tetrahydrotiazolo
- group
- guanidino
- amino
- Prior art date
Links
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- -1 cyano, benzoyl Chemical group 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 72
- BFJMHTOBRRZELQ-UHFFFAOYSA-N 3-iodo-2h-pyrazolo[3,4-c]pyridine Chemical compound N1=CC=C2C(I)=NNC2=C1 BFJMHTOBRRZELQ-UHFFFAOYSA-N 0.000 claims description 37
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
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- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000003222 pyridines Chemical class 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 5
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- CZALJDQHONFVFU-UHFFFAOYSA-N isocyanatocyclopentane Chemical compound O=C=NC1CCCC1 CZALJDQHONFVFU-UHFFFAOYSA-N 0.000 description 1
- DBBRJAWSDTYYBM-UHFFFAOYSA-N isocyanatocyclopropane Chemical compound O=C=NC1CC1 DBBRJAWSDTYYBM-UHFFFAOYSA-N 0.000 description 1
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- CWFPRSVWEWALGA-UHFFFAOYSA-N methyl 2-amino-n-cyano-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridine-5-carboximidothioate Chemical compound C1N(C(=NC#N)SC)CCC2=C1SC(N)=N2 CWFPRSVWEWALGA-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- DJASVOBLXYMZRX-UHFFFAOYSA-N n-[c-(2-amino-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-5-yl)-n-methylcarbonimidoyl]benzamide Chemical compound C1CC=2N=C(N)SC=2CN1C(=NC)NC(=O)C1=CC=CC=C1 DJASVOBLXYMZRX-UHFFFAOYSA-N 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- CABLXOSRJXFZBX-UHFFFAOYSA-N n-cyano-2-(diaminomethylideneamino)-n'-methyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridine-5-carboximidamide Chemical compound C1N(C(NC#N)=NC)CCC2=C1SC(N=C(N)N)=N2 CABLXOSRJXFZBX-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- KXXXUIKPSVVSAW-UHFFFAOYSA-K pyranine Chemical compound [Na+].[Na+].[Na+].C1=C2C(O)=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 KXXXUIKPSVVSAW-UHFFFAOYSA-K 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
- 229960000620 ranitidine Drugs 0.000 description 1
- 210000005245 right atrium Anatomy 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 208000026451 salivation Diseases 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838333514A GB8333514D0 (en) | 1983-12-16 | 1983-12-16 | Tetrahydrothiazolo(5 4-c)pyridine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8406338D0 SE8406338D0 (sv) | 1984-12-12 |
| SE8406338L SE8406338L (sv) | 1985-06-17 |
| SE455096B true SE455096B (sv) | 1988-06-20 |
Family
ID=10553370
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8406338A SE455096B (sv) | 1983-12-16 | 1984-12-12 | 4,5,6,7-tetrahydrotiazolo /5,4-c/-pyridinderivat, forfarande for framstellning derav samt farmaceutisk komposition innehallande nemnda derivat |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4624956A (en, 2012) |
| JP (1) | JPS60146893A (en, 2012) |
| KR (1) | KR910009213B1 (en, 2012) |
| AT (1) | AT391701B (en, 2012) |
| AU (1) | AU568894B2 (en, 2012) |
| BE (1) | BE901278A (en, 2012) |
| CA (1) | CA1244827A (en, 2012) |
| CH (1) | CH660739A5 (en, 2012) |
| CS (1) | CS244145B2 (en, 2012) |
| DE (1) | DE3445192A1 (en, 2012) |
| DK (1) | DK598284A (en, 2012) |
| ES (1) | ES8604603A1 (en, 2012) |
| FI (1) | FI77248C (en, 2012) |
| FR (1) | FR2556725B1 (en, 2012) |
| GB (2) | GB8333514D0 (en, 2012) |
| GR (1) | GR81232B (en, 2012) |
| HU (1) | HU193724B (en, 2012) |
| IL (1) | IL73810A (en, 2012) |
| IT (1) | IT1221007B (en, 2012) |
| NL (1) | NL8403801A (en, 2012) |
| NO (1) | NO165595C (en, 2012) |
| NZ (1) | NZ210519A (en, 2012) |
| PH (1) | PH21312A (en, 2012) |
| PT (1) | PT79681B (en, 2012) |
| SE (1) | SE455096B (en, 2012) |
| SU (1) | SU1364240A3 (en, 2012) |
| ZA (1) | ZA849770B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2173187B (en) * | 1985-03-23 | 1988-05-18 | Erba Farmitalia | Condensed 2-substituted thiazole derivatives |
| JPH03148283A (ja) * | 1989-11-02 | 1991-06-25 | Terumo Corp | チアゾール誘導体またはその塩ならびにこれらを含有する抗潰瘍剤 |
| JPH0618334A (ja) * | 1992-06-29 | 1994-01-25 | Mikuni Seisakusho:Kk | 被加熱物の温度測定装置 |
| CU22676A1 (es) | 1996-06-21 | 2001-11-16 | Univ Las Villas | Composición microcida para el control de contaminantes en procesos de producción de vitroplantas |
| US5718151A (en) * | 1996-10-01 | 1998-02-17 | Breed Automotive Technology, Inc. | Steering wheel mounting |
| AR041952A1 (es) * | 2002-11-14 | 2005-06-01 | Novartis Ag | N-sulfonilaminotiazol |
| CL2004000553A1 (es) * | 2003-03-20 | 2005-02-04 | Actelion Pharmaceuticals Ltd | Uso de compuestos derivados de guanidina como antagonistas del receptor de neuropeptido ff; compuestos derivados de guanidina; procedimientos de preparacion; y composicion farmaceutica que los comprende. |
| SG11202104132WA (en) * | 2018-11-02 | 2021-05-28 | Aicuris Gmbh & Co Kg | Novel urea 6,7-dihydro-4h-thiazolo[5,4-c]pyridines active against the hepatitis b virus (hbv) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1620508A1 (de) * | 1965-07-23 | 1969-09-18 | Thomae Gmbh Dr K | Verfahren zur Herstellung neuer 4,5,6,7-Tetrahydrothiazolo-[5,4-c]-pyridine |
| DE2205065A1 (de) * | 1972-02-03 | 1973-08-16 | Thomae Gmbh Dr K | Neue 4,5,6,7-tetrahydro-thiazolo eckige klammer auf 4,5-c eckige klammer zu pyridine |
| AR208500A1 (es) * | 1972-06-14 | 1977-02-15 | Merck & Co Inc | Procedimiento para la preparacion de derivados de oxazolo(4,5-b)-piridinas |
| CA1131226A (en) * | 1978-09-28 | 1982-09-07 | Tomohiko Munakata | Heterocyclic compounds |
| DE3134933A1 (de) * | 1981-09-03 | 1983-03-31 | Hoechst Ag, 6230 Frankfurt | "harnstoffderivate, verfahren zu ihrer herstellung und diese enthaltende medikamente sowie deren verwendung" |
| CA1260474A (en) * | 1984-12-03 | 1989-09-26 | Raymond A. Stokbroekx | Benzoxazol- and benzothiazolamine derivatives |
-
1983
- 1983-12-16 GB GB838333514A patent/GB8333514D0/en active Pending
-
1984
- 1984-12-05 ES ES538305A patent/ES8604603A1/es not_active Expired
- 1984-12-11 CH CH5893/84A patent/CH660739A5/de not_active IP Right Cessation
- 1984-12-11 GR GR81233A patent/GR81232B/el unknown
- 1984-12-11 AT AT0392484A patent/AT391701B/de not_active IP Right Cessation
- 1984-12-11 CS CS852669A patent/CS244145B2/cs unknown
- 1984-12-11 NZ NZ210519A patent/NZ210519A/en unknown
- 1984-12-11 GB GB08431161A patent/GB2153816B/en not_active Expired
- 1984-12-11 US US06/680,566 patent/US4624956A/en not_active Expired - Fee Related
- 1984-12-11 DE DE19843445192 patent/DE3445192A1/de active Granted
- 1984-12-11 AU AU36517/84A patent/AU568894B2/en not_active Ceased
- 1984-12-12 CA CA000469943A patent/CA1244827A/en not_active Expired
- 1984-12-12 IL IL73810A patent/IL73810A/xx unknown
- 1984-12-12 FI FI844900A patent/FI77248C/fi not_active IP Right Cessation
- 1984-12-12 SE SE8406338A patent/SE455096B/sv not_active IP Right Cessation
- 1984-12-13 DK DK598284A patent/DK598284A/da not_active Application Discontinuation
- 1984-12-13 IT IT24039/84A patent/IT1221007B/it active
- 1984-12-14 PT PT79681A patent/PT79681B/pt unknown
- 1984-12-14 NL NL8403801A patent/NL8403801A/nl not_active Application Discontinuation
- 1984-12-14 PH PH31585A patent/PH21312A/en unknown
- 1984-12-14 HU HU844680A patent/HU193724B/hu not_active IP Right Cessation
- 1984-12-14 KR KR1019840007963A patent/KR910009213B1/ko not_active Expired
- 1984-12-14 BE BE0/214166A patent/BE901278A/fr not_active IP Right Cessation
- 1984-12-14 NO NO845038A patent/NO165595C/no unknown
- 1984-12-14 ZA ZA849770A patent/ZA849770B/xx unknown
- 1984-12-14 JP JP59263149A patent/JPS60146893A/ja active Granted
- 1984-12-14 SU SU843824691A patent/SU1364240A3/ru active
- 1984-12-14 FR FR8419145A patent/FR2556725B1/fr not_active Expired
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